USOO887 1941B2 (12) United States Patent (10) Patent No.: US 8,871,941 B2 Lahm et al. (45) Date of Patent: Oct. 28, 2014 (54) 8-BROMO-5-QUINOLINECARBOXALDEHYDE 8,138,213 B2 3/2012 Mita et al. OXME 8,217,180 B2 7/2012 Annis et al. 8,231,888 B2 7/2012 Lahm et al. 8.410,153 B2 4/2013 Lahm et al. (71) Applicant: E.I. du Pont de Nemours and 8,513,431 B2 8/2013 Annis et al. Company, Wilmington, DE (US) 2003/0114501 A1 6/2003 Braun et al. 2005, O250822 A1 11/2005 Mita et al. (72) Inventors: George Philip Lahm, Wilmington, DE 2007/00666.17 A1 3, 2007 Mita et al. (US); Wesley Lawrence Shoop 2009/0023923 A1 1/2009 Mizukoshi et al. H11illsborough, b NJ (US); MingMi Xu,k 2009.01434102009, O133319 A1 6,5/2009 2009 PatelLahm et al. Newark, DE (US) 2010.0137612 A1 6, 2010 Yaosaka et al. 2010/0173948 A1 7, 2010 Lahm et al. (73) Assignee: E.I. du Pont de Nemours and (Continued) Company, Wilmington, DE (US) (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 CA 2252543 11, 1997 U.S.C. 154(b) by 0 days. CA 2558848 9, 2005 (21) Appl. No.: 14/275,664 (Continued)Continued OTHER PUBLICATIONS (22) Filed: May 12, 2014 Sato, et al., Science of Synthesis, 18:821 (2005) pp. IV and 924).* (65) Prior Publication Data (Continued) US 2014/0249314 A1 Sep. 4, 2014 Primary Examiner — Michael Barker Related U.S. Application Data (74) Attorney, Agent, or Firm — Pepper Hamilton LLP (63) Continuation of application No. 14/047,500, filed on (57) ABSTRACT Oct. 7, 2013, now abandoned, which is a continuation Disclosed are compounds of Formula 1, including all geo of application No. 13/561,546, filed on Jul. 30, 2012, mp s g all g now Pat. No. 8,552,218, which is a continuation of metric and Stereoisomers, N-oxides, and salts thereof, application No. 13/156,653, filed on Jun. 9, 2011, now Pat. No. 8,231,888, which is a continuation of 1 application No. 12/086,935, filed as application No. PCT/US2006/049459 on Dec. 28, 2006, now Pat. No. 7,964,204. (60) Provisional application No. 60/857,307, filed on Nov. 7, 2006, provisional application No. 60/839,988, filed on Aug. 23, 2006, provisional application No. 60/755,247, filed on Dec. 30, 2005. (51) Int. Cl. C07D 215/12 (2006.01) wherein AOIN 43/42 2006.O1 (52) U.S. Cl ( ) A', A, A, A, A and Aare independently selected from CPC A0IN 43/42 (2013.01); C07D 215/12 the group consisting of CR and N: provided that at most - - - - - - - - - - - - - - s (2013.01) 3 of A', A, A, A, A. and A is N: USPC 54.6/176 B', B and B are independently selected from the group - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 2 (58) NoneField of Classification Search each consistingR is independently of CR and H,N: halogen, C-C alkyl, C-C, See application file for complete search history. haloalkyl, C-C cycloalkyl, C-C halocycloalkyl, C-C, alkoxy, C-C haloalkoxy, C-C alkylthio, C-C haloalky (56) References Cited lthio, C-C alkyl sulfinyl, C-C haloalkylsulfinyl, C-C, alkylsulfonyl, C-C haloalkylsulfonyl, C-C alkylamino, U.S. PATENT DOCUMENTS C-C dialkylamino, CN or - NO; and R', R. R. R. 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